Wireless endpoint devices may connect to wireless local area networks (WLANs) configured on access points (APs) and WLAN controllers (WLCs) that control the APs. When roaming/mobility is properly configured on the APs and the WLCs, the endpoint devices typically do not need to authenticate to an authentication server when the endpoint devices roam; however, when roaming/mobility is not properly configured on the APs and/or the WLCs, each roaming event typically results in a new authentication attempt, i.e., a re-authentication, to the authentication server. Such re-authentications may cause overloading of the authentication server and, in a sufficiently large network environment, scalability and resource problems. Detecting/locating roaming/mobility configuration problems on the APs and the WLCs and/or the cause of excessive re-authentication of the endpoint devices is time consuming and typically requires debugging of individual endpoint devices connected with the APs/WLCs, and usually involves querying end users to generate purposeful roaming events. Overall, this troubleshooting process may take days or even weeks, and is reactive in nature.